


Helplessness Blues

by fio



Category: Supernatural
Genre: Alternate Universe, Alternate Universe - College/University, Drunk Sex, Dry Humping, Fluff and Angst, Frottage, Happy Ending, Love Confessions, M/M, Reunions, Separations, Valentine's Day
Language: English
Status: Completed
Published: 2012-02-15
Updated: 2012-02-15
Packaged: 2017-10-31 05:44:12
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 10,021
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/340571
Author URL: https://archiveofourown.org/users/fio/pseuds/fio
Summary: <blockquote class="userstuff">
              <div class="center">
  <p>    <i>I'll get back to you someday soon, you will see</i><br/>(or, the story of how Dean gets it wrong the first time around, but thankfully, gets it right on his second try)</p>
  <p>a (late) Valentine's Day fic inspired by <a href="http://homoerotics.tumblr.com/post/17367886677/mishaspulsatingpenis-baby-youre-a">this</a></p>
</div>
            </blockquote>





	Helplessness Blues

**Author's Note:**

  * Translation into Русский available: [Блюз беспомощности](https://archiveofourown.org/works/536860) by [Wintersnow](https://archiveofourown.org/users/Wintersnow/pseuds/Wintersnow)



College was supposed to be parties and girls and football games followed by more parties with more girls and the occasional class. College _turned out_ to be a whole lot of homework, sitting in a dorm room, not partying, barely interacting with girls, and watching football on a tiny TV with a roommate who listened to Enya for hours.

Dean blamed Animal House and basically every other college movie in existence for giving him such high expectations.

The roommate—who, along with having weirdo tastes in music, had a weirdo name, but he went by Cas for short—wasn't actually all that bad. Dean should've realized before coming to school that he wasn't going to be a part of the party scene since he hated dealing with... well, most everybody, but hanging out with Cas was tolerable, even if his music wasn't.

Unlike Dean, and most of their floor, Cas was an art major, so he was always covered in some kind of pencil lead or charcoal or paint, and he spent most of his time either sitting around or working in their shared room. He was quirky in a lot of ways—he always had to state the obvious; he could barely operate a phone or answering machine; he slept odd hours if he ever slept at all; he didn't blink much and had a habit of staring at people, mostly Dean, way past the point of comfort; and he had apparently only seen two movies in his entire life, Angels in the Outfield and Bambi, before Dean started forcing him to watch something from his VHS collection at least once a week. But for all his quirks, he was probably the best roommate Dean could ask for because he never brought a girl back to the room and kicked Dean out, he never made a mess he didn't clean up, and he kept mostly to himself but was always willing to talk and hang out if Dean asked.

The only really concerning thing about him was that he never seemed to go anywhere. Even Dean went to the business school's library or his teacher's office hours on weekdays, so he wasn't in the room _all_ the time—mostly because Sam called and nagged him whenever he suspected Dean was being a hermit—but Cas only left for his classes and their biweekly grocery runs. Dean had been very happy to discover during their first trip to the supermarket that Cas wasn't a health freak, which meant he wouldn't be dragged along to an entirely separate grocery store just to spend twice as much money for half as much food, plus they could go out for fast food together if the dorm food was exceptionally disgusting that day. After two months of living together, Dean had asked why Cas didn't go anywhere. Cas had stared at him for a while, then turned up his Enya and went back to his sketchbook.

Which was why Dean found it entirely unsurprising that Cas was sitting in the middle of their floor, amidst at least a dozen scattered charcoal sketches, humming along to one of his weirdo Enya tracks while most everyone else on campus was heading to a Valentine's Day party with plans to get drunk and (hopefully) laid.

Of course, Dean wasn't heading to one of those parties _either_ , but he'd at least spent two hours at the library earlier that day, in addition to attending his afternoon seminars and stopping by a liquor store. Cas rarely went to class on Friday since he only had one, so Dean was willing to bet he hadn't gone further than the bathroom down the hall.

"Hands again?" Dean asked, dumping his backpack by his desk. Cas liked to sketch body parts in dynamic poses, which looks a lot more awesome—and less perverted—than it sounds. Today was dedicated to hands.

"Mm," Cas mumbled, acknowledging him but not really paying attention.

Dean rolled his eyes, well-accustomed to Cas ignoring him while in his 'zone,' and walked over to Cas' computer to stop whatever bizarre song he had been listening to. Usually, Dean would leave Cas be until he finished whatever he was working on, or until his music got so loud that he had to start yelling at him or blast Metallica in retribution. But today was not a regular day. Today was a _special_ day, and on special days, you got drunk.

"Enough with the sketches, pal, c'mon," Dean laughed, slipping his hand underneath Cas' arm and tugging at him to get up.

"Mmph," Cas grumbled, sounding put-out, but he put down his charcoal and stood.

Dean tried to hide a smirk when Cas turned to look at him, spotting black smudges of varying sizes all over Cas' face. "Dude, how is it possible that every time you draw, you get shit all over your forehead? You don't draw with it, do you?"

Cas made a face, which stretched the smudges into exaggerated frown lines and made him look a bit like a cartoon character. "It's part of my artistic process," Cas said, which _had_ to be a joke, but he looked totally sincere, and Dean couldn't stop himself from laughing.

"Just go wash up. I'm gonna set up the Playstation."

"For what?"

Dean grinned, turning around to grab the goods out of his backpack. " _We_ are gonna celebrate with some..." he said, spinning around to present the rum and coke he'd purchased before adding with a flourish, " _epic, drunken Street Fighter_."

Cas blinked at him. "What are we celebrating?"

"Dude, it's Valentine's Day, or Single's Awareness Day, or, fuck, I dunno. _Unattached Bachelor's Christmas_. What's it matter? We've got booze and we are gonna get you drunk. And then I'm gonna kick your ass."

Cas pursed his lips, contemplating Dean's suggestion. After a minute of considerate staring, he thankfully skipped over the obvious, awkward question ("Why are two dudes celebrating a holiday about romance?") and asked, "How did you get alcohol if you aren't twenty one?"

"Fake ID, baby," Dean smiled, putting the rum down on his desk to pull his ID out from his wallet, "I've been using this thing since I was sixteen. My uncle Bobby taught me how to make it."

"That's illegal, Dean."

"Yeah, no shit. But _we_ —" Dean was careful to emphasize here that he was _not_ going to be doing this alone, because there was pathetic, and then there was _pathetic_ , "—are gonna be responsible underage drinkers, prove the stereotypes wrong, and get drunk without causing any bodily harm or property damage to anyone or anything. So go wash up already. If I stare at your face with those smudges after I get smashed, you're gonna turn into a Rorschach drawing."

By the time Cas came back, the Playstation was up and running and Dean had poured a shot for the both of them.

"To being single," he cheered, raising his shot glass in a toast. Cas sat down beside him and followed suit, clinking their glasses together before downing the rum. Dean shivered a bit, the alcohol burning down his throat, but he popped open a can of coke and washed it down before handing it over to Cas.

"Alright, man. Prepare to be owned."

The rules of Epic, Drunken Street Fighter were as follows: for every round lost, you took a shot. For every match lost, which were two to three rounds each, you took a shot. For every match lost where you didn't win a single round, you took two shots. So, if you lost two rounds in a row to lose the match, that already had you down five shots. Luckily for Dean, Cas was pretty terrible at most games, so he would have an advantage for the first few rounds, and luckily for Cas, he had the alcohol tolerance of a god and usually took about ten shots to start feeling anything _anyway_ , so he'd be better in the long run.

It only took them an hour to get thoroughly trashed and Dean decided to turn off the Playstation since he couldn't really tell what was on the screen at that point. He'd only bought the one bottle of rum, which was smart, because it was all gone and neither of them looked capable of doing any more drinking for the night. Dean fell back onto the carpet, Cas lying to his left where he was frowning up at the ceiling.

"Whazzit?" Dean slurred, wondering what Cas was doing.

"The dots on... the brother... I mean. _My_ brother... he wouldn't like... those dots," Cas explained slowly, though what he was saying made no sense whatsoever. Dean let it go, already forgetting that he'd asked ten seconds ago. They lay on the floor in companionable quiet for a while after that, neither one moving much for fear of unsettling their alcohol-filled stomachs.

"I am... very, very drunk," Dean said, interrupting the quiet and rubbing a hand on his chest. His insides felt warm, in a comfortable sort of way.

Cas turned his head to stare at Dean who turned to stare back.

"Yeah. 'Cause... lots of rum," Cas said, too drunk to talk in more than a few words at a time.

Dean was about to complain about Cas pointing out the obvious again but stopped short, thought process coming to a loud, screeching halt as he took in Cas' bright, blue eyes. But he didn't get caught in them for long, and he found his eyes repeatedly going down to Cas' mouth, which was weird, because Cas' mouth was... well, _Cas' mouth_. And he didn't remember it looking that kissable before. Or maybe he did, but just pretended he didn't. He really wanted to try it now, though. He wondered if kissing him tasted like Cas' sketchbook always smelled, a weird but pleasant papery scent.

"Dean?" Cas whispered, scooting a bit closer. Dean's brain jump started and he realized time was still moving and Cas was still sitting beside him, talking to him, calling his name.

"Dean, you o—" Cas started when Dean still didn't say anything, only to be silenced by Dean surging forward and kissing him hard on the mouth.

He was wrong. Cas tasted like rum—which made more sense than him tasting like paper, if Dean stopped to think about it, but he had no plans of stopping. Cas' mouth was wet and soft and, after the initial surprise, eager to kiss him back. Dean's right hand lifted off his chest and reached over, sliding up Cas' neck into his hair. The way Cas shivered underneath his touch was enough to make Dean moan against his lips before pushing his tongue forward, slipping it into Cas' mouth and tasting the remaining sweet tang of rum on his teeth. Cas' hands found Dean's side, fingers burying into his t-shirt and tugging at him. The touch tickled a bit, and Dean smiled into the kiss, pushing himself off the floor with his left elbow and rolling on top of Cas without pulling his mouth away.

He was already starting to get hard in his jeans, and he rocked his hips downward, rubbing himself against Cas' thigh. His drunken brain didn't register that the lower half of a guy was definitely going to be different from the lower half of a girl until after he felt Cas get hard too and start pressing back up against him.

Dean pulled away from the kiss—and oh god, did he regret that already, because Cas tasted really good and he felt really good and looking at him now, his lips all red and swollen and his face burning pink and his eyes so damn _bright_ , made Dean's dick throb and a small whimper slip out of him. His hand was still in Cas' hair, fingers running through it and tickling at Cas' scalp. He couldn't make himself stop, even if he wanted to, loving the feeling of Cas' hair against his skin and the look of Cas beneath him.

"Dean?" Cas asked, hands now on either side of Dean's waist, gripping him gently enough to let him go without a fuss, but still hard enough to tell him Cas didn't _want_ to let go.

"I... I've never..." Dean started, but didn't continue, not sure where that thought was going.

He'd never been with another guy, which was true. And he'd never thought of being with another guy, at least out loud or while sober. And he'd never thought he'd do this with _Cas_ , but mostly because he had thought Cas was uninterested in sex with anyone.

"It's okay," Cas said, and he smiled, rolling his hips up off the floor and pushing his cock against Dean through the denim of their jeans, and Dean moaned, both from the rare sight of Cas' smile and the sudden and immediate need to get the both of them out of their pants. "Dean, 's okay," Cas said again, and Dean leaned back down to kiss him, because he believed it. This was okay. This was good.

Dean reluctantly took his hand from Cas' hair to address the more important matter of getting his jeans undone. Cas followed suit, his hands dropping from Dean's sides to help himself out of his pants. With the both of them being _very_ drunk and determined to keep kissing the whole time, getting their jeans pulled down enough to expose their boxers was a bit of a battle, and there was no way they were getting them completely off. Dean was fine with his jeans still being halfway up one of his legs, and Cas didn't bother trying to get his all the way off his ankles because he could just cross them and settle them around Dean's waist. And Dean was more than happy with that position, because it pulled them closer together, their cocks rubbing against each other with much less in the way now that the layers of denim were gone.

Still not sure what he was supposed to be doing, though Cas hadn't stopped him yet, Dean decided to try out rocking them both together, thrusting his hips forward like he would with a girl. Cas was the one who pulled away from the kiss this time, dropping his head back against the carpet and exposing his neck as he gasped, eyes slamming shut, and his hands grabbed desperately at Dean's shoulders.

"Was... was that good?" Dean asked, his hand reaching up to take its place back in Cas' hair.

Cas groaned, eyes still shut, and pulled at Dean's shoulders hard, his legs squeezing around Dean's waist and forcing their cocks together. He was apparently past the point of using words because he stayed silent aside from quiet moans as he rubbed up against Dean in a frantic, desperate pace.

"So... yes," Dean said, answering his own question and using his other hand to grab Cas' waist and hold him down. Cas whined up at him for being forced to stop and Dean laughed. "Slow down, 'm still new at this."

He thrust forward again, moving both of them together, licking his lips at the sight of Cas' mouth falling open all over again. He started moving just like that, in a slow rhythm to get the hang of it, rubbing their erections between each other's bellies with delicious, steady friction. Each drag of skin against damp cloth against skin made Cas' jaw drop open and breathe a bit heavier, and Dean was already feeling himself coming undone after only a few minutes of quiet, quick movements together. He wondered what it would be like to get their boxers out of the way, or to be _inside_ Cas. His eyes slammed shut at the thought and he gasped, hips rolling down sudden and faster than they'd been moving a second ago, making Cas moan in surprise. Everything was so hot, the both of them sweating through their shirts and against each other, but Dean knew going one step further, being _in_ Cas would be so much hotter, enough to drive him crazy. He jerked forward again, feeling his balls tighten and colors start to explode behind his eyelids. His pace wasn't steady or slow anymore, and he was rubbing down against Cas faster and faster every second, and he was so close he could barely _breathe_.

"Cas, 'm gonna—" he hissed, struggling to form the words.

"Yes, _God_ yes," Cas breathed and with that, Dean came, fingers tightening in Cas' hair and wetness spilling out inside his boxers against his skin. Beneath him, Cas kept moving in a fast rhythm even as Dean slowed down to a stop, coming with a soft cry and a shudder.

Dean felt heavy and content, and as he got his breath back, he started kissing Cas' neck, licking at the salty skin and rocking their hips together with the occasional thrust, milking the last of their climax as long as he could. Cas' legs dropped from around Dean's waist to fall shakily back down onto the carpet and his hands slowly relaxed, letting go of Dean's shoulders so he could reach his arms around and hang over the back of Dean's neck.

They didn't say anything, content to just breathe and stay pressed together, the warmth and afterglow enough to make them ignore the awkward stickiness covering their skin. Dean eventually slid himself off of Cas, but only halfway, keeping an arm over his chest and one of his legs between Cas' thighs. Cas pulled one of his arms back to his side but left the other stretched out, cradling Dean's neck. They fell asleep like that, too drunk to care to clean up or move to one of their beds.

Neither of them said goodnight, but when Dean was starting to drift off, he could feel a soft kiss against his mouth. But he wouldn't remember.

***

The morning after drinking usually consisted of a hangover and an attempt to piece together the jumbled bits of the evening that could still be remembered. The day after Dean drank with Cas, however, was filled with nothing but painful, terrifying clarity.

"Oh. Fuck," Dean said to himself with a growing sense of horror.

His boxers had dried and crusted while he slept and he was holding himself over a passed-out Cas, whose boxers looked equally crusty, which could only mean what he was remembering was, in fact, last night and not one of his dreams. Which meant he had just hooked up with his roommate. His _guy_ roommate.

"Oh, fuck," he said again, his stomach twisting and a sudden need to vomit overtaking him. He grabbed his door key and fled the room, bursting into the bathroom and startling a kid named Andy, who was another business major and lived four rooms down the hall, as he found one of the stalls and slammed the door shut before he began to wretch.

"Crazy night, huh?" Andy laughed while washing his hands. Dean grumbled in response before emptying his stomach of what had to be half of the rum he drank last night. "Man, you really don't sound good. Want me to get Cas?"

" _No_!" Dean said immediately, making Andy flee the bathroom.

Dean was so _fucked_.

After about half an hour in the bathroom and having revisited every thing he ate and drank in the last twenty four hours, Dean still felt wobbly, but stable enough to get back to the room. Even though he really, _really_ didn't want to go back.

Making his way down the hallway felt like it took an eternity and hovering in front of the door, deciding whether or not to actually unlock it and walk in, took another eternity. Eventually he forced himself to push it open and step inside, and he was greeted with the sight of Cas, sitting up and pulling open his boxers to frown at the mess inside. At the sound of the door, he looked up, and the two of them stared at each other in silence.

Dean was the one who broke it.

"Cas, I—"

He could see Cas suck in a breath, and for a moment, he thought Cas looked hopeful. But the longer he hesitated, the more that look turned into fear, and Dean convinced himself that Cas was only hoping that Dean was as eager to forget what just happened as he was.

"I... don't really remember. What happened last night, I mean."

Cas kept staring at him, still holding his breath.

"I... I can guess, but... I can't remember. I. I can't."

He was lying—he wouldn't ever forget about the night before—but the last bit was true. He couldn't. He couldn't be with a guy. Not in Kansas, not with his father who looked down on him and his little brother who looked up to him. He only wished his drunken foray into experimentation had been with someone he didn't know. Someone who he didn't know liked Enya and other weirdo music, who he didn't know could paint such amazing shit that it belonged in a museum, who he didn't know smiled only when he really, truly meant it because he only bothered with getting to know people who he felt were worth the trouble. Dean had a sinking feeling Cas was going to regret making that mistake about him.

After another few moments, Cas let go of the breath in his lungs and stood up, legs looking as wobbly as Dean's felt, and walked towards the door.

"Cas, I—" Dean started again, though he didn't know what he was going to say. He didn't get a chance to figure it out. Cas stared at him, blank and empty, and Dean had no words left to say. He moved out of the way and let Cas get to the door, stepping out and heading down the hallway, leaving Dean alone with his crusty boxers and a sick feeling in his stomach.

That was the last time Cas looked at him.

***

Freshman year ended three and a half months later.

The rest of the semester went by painfully fast and Dean spent most of it alone. He still went to all his classes, but he stopped going to the library and office hours, hoping to catch a glimpse of Cas, but Cas only came back to the room to sleep late at night if he came back at all, and he always left early in the morning, before Dean could see him. He didn't bring his sketchbooks or his paints or his charcoal to the room anymore and Dean figured he must have found some corner of the art building to set up as his own. He sometimes wondered if Cas irritated anyone else with his Enya crap or if all art students loved that kind of thing.

During finals week, Dean reluctantly made his way to the library every day, knowing that he wouldn't get any studying done if he just sat in the room looking at all the things that reminded him of Cas, and every day he came back and more and more of Cas' things were missing until he was completely moved out.

The official freshman move out day was actually the Sunday after finals, but the last trace of Cas was gone by Wednesday.

***

"You. Are. Pathetic."

"Gee, thanks a lot, Sammy."

"I'm just being honest with you, Dean, and stop calling me Sammy. I stopped being twelve eight years ago."

"Whatever you say, _Sammy_."

There was a loud, heavy sigh on the other end of the line. Dean smirked.

"Stop smirking."

Dean rolled his eyes and kicked his feet up on his desk, "It's really creepy when you do that, y'know."

"Whatever. Look, just. Just come out tonight. Please?"

"No, dude, I'm single on Valentine's Day and I'm sick of having it rubbed in my face. I'm not interested in any more blind dates with Jessica's friends or friends of her friends, and I am _not_ joining you guys for dinner. I refuse to be your third wheel. Plus you guys have terrible taste in restaurants."

Sam made an amused noise and said, "Wanting to go somewhere that serves more than 'heart attacks on a bun' does not mean we have terrible taste."

"Yeah, says you," Dean grumbled, but he was smiling. Talking to Sam always cheered him up, and he could use it on a day like today. Valentine's Day and the day after were still sore spots, even ten years later.

There was a tap on his window and Dean looked up to see Michael staring at him from the doorway.

"Uh, I gotta go. Have fun tonight," Dean said, pulling his legs off his desk and leaning forward in his seat. Before putting the phone back in the receiver, he held a hand up to hide his mouth from Michael and whispered, "And remember to use protection."

" _Dean_ —" Sam squawked into the phone, but Dean hung up before he could hear him get _really_ indignant.

"Sorry 'bout that, Michael. What's up?"

Dean's boss was a very straight-lace, serious guy who was very serious about rules and being on time and crap like that, but he told everyone to call him by his first name, regardless of formal policy. It was weird, but Dean wasn't about to tell the guy who paid him that he was strange. At least not to his face, anyway.

"How're the reports today?"

"Uh, good. Mostly done."

"Good. Come with me."

"O-Okay."

Meeting with Michael usually never meant anything good, but Dean was a special case. A lot of people in the firm who worked under Michael thought Dean had found some way to suck up and was now the office favorite. Dean didn't really give a fuck what everyone around the office thought, but he was pretty curious about how this had happened, too. He didn't know if it was even _possible_ to suck up to Michael, since he was such a stickler for formality and following rules, but he'd always favored Dean since he got hired as a financial analyst a few years back and Dean had no idea if it was something he'd done or if Michael was hot for him or what. It made him a bit uncomfortable, getting favored like that when he didn't do anything special, but Michael didn't sexually harass him or anything and as long as he was signing Dean's paycheck, he wasn't going to make a fuss.

Inside Michael's office, there was a startling contradiction. Inside all of the order and finery of Michael's office sat a hippie. A hippie with paint and food stains all over his clothing who hadn't shaved in a day or two and looked pretty stoned to boot.

"Uh, who's that?" Dean asked, unable to stop himself from staring.

"This is my brother," Michael said with a heavy sigh and Dean felt himself wince. He knew enough about strained family relationships to tell that this was one of them—when Sam had chosen to go to Stanford instead of KU like the rest of the family, everyone just stopped talking for a while until Dean got a job out in LA and Sam called to congratulate him. It didn't take long for things to go back to normal after that.

"He looks..." Dean trailed off, not sure how to end that without offending somebody.

"Horrendous, I know," Michael finished for him.

"Well, I wasn't gonna say _that_ , but. He is a bit... out of place."

"He's been hired to paint something for our building's lobby on the first floor."

"Oh. He's a painter. That would explain the paint all over him, then."

"I have work to do, so I was hoping you could show him around instead. Take him on a tour, let him get a feel for the atmosphere. We don't want a painting of a deer in a forest or something if it doesn't match the color scheme, right?"

Dean didn't understand that at all, but he nodded and said, "Uh, yeah, of course."

"Great," Michael smiled, and he looked like an evil mastermind whose plan had just fallen together, but then he was back to frowning as he stepped towards his brother and Dean figured he'd imagined it.

"Good news, I've found someone to show you around. Now get out of my office. And for Christ's sake, _keep your shoes on_."

Michael's brother heaved a heavy sigh and pushed out of the cushy chair he'd sunken into, slipping his feet into the sandals he'd kicked off. "Right, right, leave it to your little minions," he said flippantly as he walked towards the door, not noticing Dean standing right in front of him. Michael waved a hand at them both and Dean stepped out of the way so he wouldn't get run into and pulled the office door shut. The hippie was already down the hall, halfway to the elevators, and Dean ran to catch up.

"Who're you calling a little minion, pal?" Dean whispered, grabbing him by the arm and stopping him mid-stride.

The guy's eyes locked in on Dean's face for a moment and widened, looking surprised and horrified and ecstatic all at once, before they dulled in an instant and roamed his face like it was a blank sheet of paper he found no interest or purpose in. But Dean knew that color and he knew that look. He _knew_ , but he convinced himself it was impossible, letting go and watching the guy walk the rest of the way to the elevators. He didn't get his answer, but he didn't want that one anymore.

"Michael didn't tell me your name," Dean said once the elevator arrived and they stepped in. They were on the twelfth floor and had a ways to go before they reached the lobby. Dean hoped no one else would need to head downstairs in the next few minutes.

"He didn't tell me yours, either," the guy said with his back to Dean.

"I asked you first."

"You didn't ask me, you said Michael never told you."

"Fine. What's your name?"

"What's yours?"

"It's Dean. Dean Winchester. Now what's—" Dean started, but the elevator interrupted with a loud ding and both of them flinched. Dean looked up and saw they were only at the third floor as the doors opened and several people filed in. He wanted to ask if they were _really_ so lazy that they couldn't take the stairs, but he bit his tongue and waited for them to get to the bottom floor.

The moment the doors opened, everyone filed out and Dean saw the painter leaving, too, but he grabbed him by the arm and pulled him back in, hitting the top button and not letting go until the doors slid shut.

"What the hell—"

"Look, if you won't tell me your name, then I'll tell _you_. Your name is Castiel Milton but you go by Cas for short and you went to KU ten years ago and you were my roommate for a year and you used to listen to really shitty music and you never watched any movies so I had to make you watch mine and you sucked at video games no matter how hard you tried and you never could use a phone right so you probably suck with a cell and you were always drawing or painting and you got covered in whatever you were working with and I don't know if any of this stuff is still true because I haven't seen you in ten years, but I haven't forgotten any of it, Cas, not a single thing."

Dean was breathing hard by now, having just sputtered nonstop for a whole minute, and he hoped he hadn't made a mistake, because if he did, he just made a complete ass out of himself in front of his boss's brother, but if he didn't, if it _was_ him—

"You remember me?" Cas asked, eyes going wide. Dean smiled, and then he laughed and doubled over, and then he fell back on his ass and sat there on the floor of the elevator, laughing like a lunatic while Cas hovered over him in concern.

When he got his breath back, he looked up and gave Cas a weary smile.

"Yeah, I remember you, Cas. I remember everything about you."

***

It took Dean quite a while to convince Cas that he was fine, because cracking up in an elevator over reuniting with your old college roommate isn't exactly normal, but he managed to do it eventually. Once they made it back to the bottom floor, they walked around the building together, letting Cas get a feel for the color scheme or whatever Michael had told him to do while Dean filled him in on his life post-graduation. Cas was quiet, taking in everything with nods and short mumbles to confirm that he was listening. Dean wasn't sure how much Cas remembered, or was even willing to remember, so he didn't bring up school again, but Dean wondered if he was boring Cas with all his blabbering about his job, because it wasn't very interesting to himself.

The tour went on for a little over an hour and Dean figured he was free to go back to work once they were done, but he didn't want to leave. Not when he'd finally found Cas again.

"Hey, um," Dean started once they got back to the twelfth floor, making Cas stop before walking back to Michael's office. He kept his focus on the window, and Dean realized Cas hadn't looked him in the face since helping him off the elevator's floor. "Michael pretty much gave me the rest of the day to help you, but if we're already done... Do you want to maybe get a bite to eat, or grab a drink somewhere?"

Cas did look at him then, but Dean barely stopped himself from flinching and looking away. The smile Cas wore now was bitter and rueful, and Dean knew exactly why.

"Are you sure you want to invite me out to get drunk? I was under the impression that you thought you'd made a huge mistake last time that happened."

"No," Dean said, fast enough that Cas' crooked smile was wiped away by surprise, "I know I made my worst mistake the day after."

They stood in silence for a few minutes, oblivious to the office happenings—and curious whispers—still going on around them, and Dean held his breath, waiting for Cas' answer. He felt an echo back to the last conversation they'd had back at school, and he realized he was on Cas' side of it this time. He felt _terrified_.

"You... _do_ realize you're asking me out on a date, right?" Cas asked after a while, sounding stunned, and Dean's breath rushed out of him with a whoosh before he started to laugh.

"Yeah, I do."

"I mean. _Me_. You're asking _me_."

"Do you want to go or don't you?" Dean asked, still laughing.

"Yes," Cas answered, looking a bit hesitant. Dean stepped forward and draped an arm over his shoulder, giving him a grin.

" _We_ are gonna celebrate. I've got booze, but no Street Fighter this time."

Cas blinked up at him before giving him a smile in return.

"What are we celebrating?"

"Our reunion, of course."

***

Dean took Cas to the fanciest restaurant he could get them into without a reservation but spent most of their dinner playing footsie underneath the table instead of paying attention to his excessively expensive food. It was Cas' turn to talk about what he'd done the last ten years, and Dean was unsurprised to hear he spent most of it being a jobless bum—the whole hippie look he was rocking was too convincing to be anything but authentic—before his older brother Gabriel used one of Cas' abstract art pieces for part of a set on one of his shows. After that, he started getting commissions left and right. This job with Dean's firm was actually Michael's attempt to keep Cas from getting drawn in by what he called, "seedy Hollywood types," which Gabriel was already a part of.

"Michael's protective of you, huh?"

"Yeah, since I'm the youngest brother. Gabriel's already a lost cause, so he's afraid I'm headed down the same path. But he does it in these weird ways like making me do work for him, dragging me into student government as soon as I could join it, or forcing me to organize my sisters' shoe closets while we grew up. Apparently teaching me 'order' and 'discipline' was his way of preparing me for the rest of the world and keeping me away from the unsavory types."

"Those lessons really stuck with you," Dean snorted and Cas laughed.

"You'd be surprised. I was pretty straight-lace, just like him, until I escaped to college. Then I got to room with you and just... stopped caring about 'order' and 'discipline,'" Cas said. Dean froze, feeling his face get hot. Across the table, Cas bit at his lip and leaned forward in his seat, sliding his leg against Dean's. "Um, I know you invited me out for a drink after this, but—"

"You want to skip it and head back to my place?"

"Yes. _God_ yes."

Dean nearly tackled the waiter to get the check.

***

They were careful to keep their hands in their pockets on the walk back to the parking garage, and Cas thankfully kept his hands in his lap while Dean was driving, because Dean was having a hard enough time focusing on the road as it was. He stayed off the freeway, knowing traffic would be getting ridiculous about now, and took the back streets all the way to his apartment. When they finally made it into his apartment building, they saw a small crowd of people around the elevators and went for the stairs instead. They made it up about half of one flight before Dean grabbed Cas by the waist and pushed him up against the wall, kissing him hard and hungry. Cas' hands went for Dean's ass, tugging him forward and rocking them together. The scratch of Cas' beard was unfamiliar but welcome and Dean reached a hand up to stroke a thumb over the roughness of his stubble as they slid their tongues together.

After a few moments, Dean had to pull away for air. Cas looked up at him, breathing heavy, and Dean smiled, leaning their foreheads together. "I've been wanting to do that again for ten years," he said, keeping his voice quiet so it wouldn't echo up the stairwell.

"Me, too," Cas whispered back, and Dean surged forward, kissing him with urgency and need. "Upstairs, Dean, upstairs," Cas reminded him between kisses, and Dean grabbed him by the thighs and lifted him up, keeping their lips moving together as Cas' legs closed around his waist.

It was a bit harder than he thought to carry a grown man up the stairs, but he only lived three stories up. "A rich, business-type like you only lives on the third floor?" Cas asked when Dean had to stop kissing him so he could keep breathing.

"I'm a modest man," Dean smiled, pushing open the exit door when they reached the right floor.

"Modest enough to drive that flashy, old Impala around downtown LA?"

"Hey! Don't you call my baby old, dude, I will drop you right here."

"And what, go sleep with your car instead?"

Dean's eyes narrowed for a moment before he shook his head, "No, too messy. I can't sully my baby like that. But, uh, do me a favor and grab my keys out of my pocket? We're here."

Cas smirked and reached both of his hands into Dean's front pockets, squeezing his legs before pulling out the key and handing it over. Dean unlocked his door and pushed it open, kicking it shut behind him and walking them straight to the bedroom, hitting the lights on as he went. Cas dropped down onto the bed with a soft bounce and Dean followed down after him, hands going for Cas' shirt immediately while Cas used a finger to undo Dean's tie. The momentum they had built up on the way back to the apartment had been burned up by their kissing in the stairwell and now they were both content to take their time, the want between them a slow burn.

Dean helped Cas pull his shirt the rest of the way over his head and tossed it onto the floor, sitting back on his knees to let Cas lean up and start opening up his own shirt, button by button, while Dean slid his jacket off and let it join the growing pile of clothes beside the bed. When Dean's shirt was completely undone, Cas didn't try to pull it off of him immediately. Instead, he slipped his hands beneath the open sides to roam slowly over Dean's skin, starting at his ribs and dragging fingertips down to his hipbones. Dean's breath hitched at the touch, his stomach fluttering beneath Cas' cool thumbs as they stroked over his hips.

"That tickles," Dean laughed, bringing their foreheads together, and Cas chuckled, pushing upwards to kiss Dean soft and slow.

Cas' hands moved from Dean's skin to his belt, working the belt buckle and slipping it out of the belt loops with his eyes closed and his mouth still locked with Dean's. His fingers went for the zipper next, tugging at Dean's slacks and pulling them down his thighs, but when he want for Dean's underwear next, Dean grabbed hold of his wrists and stopped him. Cas broke the kiss to stare at Dean, confused.

"Not just me. Your turn," Dean explained, tugging his shirt off at last and dropping it on the floor, followed by his shoes as he toed them off. Cas smiled, kicking his sandals off and leaning back down onto the bed, giving Dean room to tug his slacks the rest of the way off his legs. Down to his socks and his boxer-briefs, Dean crawled back over Cas on his knees and spread his hand across Cas' skin, amazed at how cool he was to the touch. He marveled at it for a moment more but made himself focus on the task at hand as he went to undo Cas' pants. They weren't sweatpants, but they certainly weren't slacks or jeans, either. Dean wasn't sure how to describe them, but it wasn't important. What _was_ important was how easy it was to slip Cas out of them, and Dean was only half-surprised to find Cas hadn't been wearing underwear underneath. His cock was already hard and Dean wrapped a hand around it and squeezed. Cas made an appreciative noise and reached for the band of Dean's boxers again, but Dean stopped him again.

"Why not?" Cas pouted and Dean paused.

"I... " Dean tried to say, but bit at the inside of his cheek and stayed quiet.

"You don't want to?"

" _No_! I mean, _yes_ I want to, it's just... I still haven't..."

"Still haven't what?"

Dean dropped down onto Cas and let out a frustrated groan against his shoulder. "I still haven't done more than what I did with you. With a guy, I mean. I'm not a _virgin_ , but—"

"You've never been with another man aside from me?"

"No," Dean mumbled, feeling his face and ears burning as he blushed against Cas' skin, "I've tried, gone to clubs, gotten all the way back to a guy's place before, but I couldn't do it. Not when they weren't you."

Cas was quiet for a minute, but it felt like an eternity while Dean lay there on top of him, face hidden in the crook of his neck, waiting for him to say something.

"Dean," Cas whispered, pushing at Dean's arms until he lifted himself up to meet Cas' eyes, "it's okay." Cas' hands slid up Dean's arms and up his neck to settle on either side of his face, thumbs stroking at his cheeks as he smiled wide. "It's okay. It's you and me this time. Only us."

The want that had settled between the both of them, a slow burn of need, suddenly flared and Dean couldn't get his mouth on Cas fast enough.

Everything exploded with heat, every inch of Cas' skin that Dean's fingers found was hot to the touch and his tongue and his lips were searing against Dean's own. This time, when Cas' hands went for Dean's boxers, Dean didn't stop him, and once he was free of them, his own hands found Cas' hips and pulled them flush against his. Cas' legs spread out, making it easy for Dean's cock to slide together with Cas', the heat of it alone enough to make Dean hiss and cry out. Their hips moved in a rhythm just like that, impatient and needy for more friction and more feeling, while they kept kissing, tongues dancing with and around each other.

Without warning, Cas reached between them and took Dean's dick in his hand, stroking it with a tight fist a few times, fingers now wet with precome. Dean groaned, hips stuttering to a halt as he let Cas work him, but Cas didn't continue for long, instead pushing at him until he was pressed up against the back of Cas' thigh.

"Cas, what're you—" Dean panted, but his sentence fell apart into a breathless moan when Cas slid his cock up against his hole.

"I want more," Cas whispered, and that was all Dean needed to hear.

"In the drawer," Dean instructed, mouth moving from Cas' lips to cover his neck in bites and kisses. Cas reached a hand towards the bedside table, moaning when Dean laved at his adam's apple with a burning tongue, and rooted around the drawer for a moment before pulling back with lube and a packet of condoms which he promptly pushed against Dean's shoulder. Dean let go of Cas' waist and reached up to grab them from Cas before sitting back on his knees. Cas wrapped his legs around Dean's hips, squeezing and keeping his ass pressed against Dean's cock and making it _very_ hard to concentrate.

"Cas— Cas, hang on a sec—" Dean said, wincing at a particularly hard roll of Cas against him. He was still fumbling with the condom wrapper while Cas was using him like a stripper pole, which he would normally be _totally_ okay with, but right now he wanted more than that. "Cas, slow down, I gotta—."

"Here," Cas hissed, grabbing it from Dean, ripping the package open with his teeth and handing it back to him, "Now hurry up."

Dean's brain shorted-out for a second at the sight of that, but he snapped out of it quickly and worked the condom over him with ease. He recognized this part, but realized he didn't know what came next. "Um. I don't—"

"Lube plus fingers inside me. You can do it," Cas reassured, one of his hands wrapping around the base of his cock and squeezing to keep himself from shooting off too soon. Dean went for the lube immediately, clicking it open and pouring half the bottle out onto his hand. Cas had stopped rocking down against him so Dean could pull his legs up onto his shoulders, giving him a better angle to reach down and push in his first, lubed-up finger.

It was warm and tight and a lot easier than Dean had thought it would be. Watching Cas start to squirm against the sheets, Dean had a hard time stopping himself from slipping in two more fingers now just to see how much Cas liked it. But he wasn't going to fuck this up—not this time, not again—and he took his time, waiting until he felt Cas loosening up enough for him to use another finger.

" _Ah_ , Dean," Cas keened, tightening around the three fingers Dean was working inside him, and that snapped the last of Dean's restraint. He slid himself free and dropped Cas' legs back down to the bed, using his lubed up hand to work his cock with a few readying strokes before lining himself up with Cas and pushing forward, inch by tantalizing inch. "Fuck— Yes, _Dean_ ," Cas whined as Dean slowly settled all the way inside him, stretching him open.

It was awesome, being deep inside Cas like this, and not just awesome like a deal on ties or free pie. It was so awesome that Dean couldn't keep his mouth from dropping open and it felt like the wind had been knocked out of him. He wanted to start a religion around this feeling. He didn't really care what it was called or what the rules of it were as long as everyone knew that being here, feeling _this_ , sinking into Cas' heat and Cas' legs wrapping around your waist to help you sink even deeper, was better than anything God could give you. And Dean really didn't care if God struck him down for blaspheming right now, because he would never feel more amazing than he did right now.

"Please, please, please," Cas was mumbling, pulling Dean out of his thoughts. Dean had been lost in his own pleasure and wasn't really sure what Cas was asking for, but he moved his hips forward gently, unable to keep still anymore, and Cas' back lifted up off the bed as he let out a satisfied moan.

"Like that?" Dean asked, moving forward again. Cas wrapped his arms around Dean's neck and nodded into his shoulder, past the point of words.

Dean slid himself out, then pushed back in, going slow and giving them both time to adjust. Every thrust in had Cas moaning, and every pull outward had him gasping, and Dean was amazed that such a quiet guy was capable of making this much noise. It made it hotter, his ears burning and his mind going fuzzy at the mix of sensations, Cas' sounds and Cas' heat as Dean pushed in again and again and again. Dean himself was breathing hard already, even though they were moving at a slow, even pace. His hands were wrapped around Cas' hips, reaching down and squeezing his ass, pulling him closer for Dean to sink inside. Watching Cas' face was a treat, the way his features tightened and relaxed every time Dean hit deeper, but Dean could barely hold his head up any longer and he dropped down to press his forehead on the sheets beside Cas' neck.

They rocked together like that for a long time, Dean thrusting into him at a gradually quickening pace, and a coil tightened in the pit of Dean's belly, threatening to explode if he didn't go faster. After a while Cas started moaning at him, trying to get his attention instead of just telling Dean how he was feeling.

"Mm, what?" Dean mumbled, biting at Cas' shoulder. Cas arms fell away from Dean's neck and reached down, grabbing at his thighs and pulling him closer. "You close?" Cas nodded, panting hard, and Dean thrust forward hard once, listening to Cas fall apart and feeling his legs start to shake around his hips.

"You want more... like _this_?" Dean asked, punctuating the word with another hard push inside and Cas' back arched up off the bed, pressing him flush against Dean's chest. His hands fell away from Dean's thighs and grabbed at the sheets beneath them, no more sound coming from him even as his mouth fell open with each push. Dean started moving faster and harder, desperately wanting to push Cas over the edge and watch him fall to pieces, the coil in his own belly threatening to snap. The headboard hit the wall with a loud thump when Dean thrust in particularly hard, and Dean realized absently that his neighbors would know exactly what he was doing—if the noises Cas had been making hadn't been hint enough already—but he couldn't slow down or stop now and he kept going faster and harder, the loud thumps joining the sounds of Dean's heavy breathing and skin slapping against skin.

It didn't take long for Dean to start feeling like he was going too fast, pushing too hard, but Cas kept making silent moans and pressing his ass back against Dean with every slide inside, even though Dean was sure Cas was going to be sore and bruised in the morning after how hard he was going. But if Cas didn't like it, Dean was sure he would know by now, and neither of them were _there_ yet—they were close, but not close enough—so Dean couldn't bring himself to stop.

His hands were still on Cas' ass, squeezing and pulling him closer, but it wasn't enough, he still wasn't close, even with the pressure inside his belly slowly driving him mad. He thought back to the last time they'd done this, their first time, how just _thinking_ about being here, like this with Cas, had pushed him over the edge. He let out a groan and let go of Cas' skin to reach up and bury a hand in Cas' hair, remembering the feeling of it ten years ago, and suddenly, everything was _right_. Cas came with a loud cry after a few more thrusts, his cock throbbing between them and coating their chests with come, as Dean's fingers combed through his hair and Dean still pushed his way inside him, the headboard banging so loud they'd probably be getting complaints tomorrow. His back stiffened and his legs clenched hard around Dean's waist before easing slowly and trembling as he held on. Dean was so close, Cas' even tighter and hotter around him now, and he felt like he was going to _explode_ if he didn't get off soon, but he wasn't there, not just yet, until—

" _Dean_ ," Cas hissed, and the coil burst, undoing him from the inside out. His vision went white and his balls were tight against Cas' ass as he came, shuddering and pumping the last of himself out with hard, staccato thrusts, each one punctuated by the sound of the headboard against the wall.

Dean's ears were ringing by the time he was completely spent, but it sounded like the entire world was applauding them, as awed and grateful for their climax as Dean was himself. He collapsed down on top of Cas and panted hard against his neck, unable to open his eyes or form words. His fingers were still holding onto Cas' hair, but he couldn't concentrate hard enough to make them move or pull them away. Beneath him, Cas finally unlocked his ankles from behind Dean's waist and dropped his legs out onto the bed, hissing as he did it.

That snapped Dean back to himself, but at first all he could was grunt, and then, after a few more tries, he managed, "You sore?"

"Mm. Good sore, though."

"Okay."

After a while of just lying there, sticky and sweaty and _very_ content, Dean eventually found the energy to push himself off of Cas' chest and pull himself out, sliding off the bed to make a quick run for the bathroom. He tossed the condom out and came back with a towel, crawling back onto the bed to give them both a quick wipe down.

"You sure you're okay?" Dean asked, hand pausing over Cas' chest.

"Yes, Dean, I'm fine. Tired, though."

"Me, too," Dean said, followed by a yawn. He threw the towel onto the floor with the rest of their scattered clothes and slid off his socks—he was a bit embarrassed to realize he hadn't taken them off earlier, but Cas didn't look like he cared—before pulling the sheets down and helping Cas slip underneath them. He got up one more time to turn off the lights, then settled in under the covers, too.

"Hey, Cas," Dean whispered, even though Cas already looked like he was passed out.

"Hm?" Cas mumbled back, keeping his eyes closed.

There was a lot Dean wanted to say, but he had no idea how to put it into words. He kept trying to figure out the best way to say, "So, I was a giant dick and I've actually been pining for you for ten years which is why I've been single for a decade even though my brother and his girlfriend think it's pathetic but nobody they set me up with has ever measured up to you and I know that I'm this corporate dick now but I am totally cool with you being a hippie—hell, if you want me to quit my job and go live on a farm or something, I'm totally down for that—and I know I fucked up the first time and I know it was cruel but I won't this time, I promise, so would you maybe, please give this thing a shot with me?" But everything he came up with just sounded wrong and jumbled in his head, and he was so afraid that Cas would say _no_ that he couldn't make himself say anything at all. After a minute, Cas blinked open his eyes in the dark and scooted closer on the bed, their legs tangling together underneath the covers.

"Dean?" Cas prompted, when Dean said nothing, and all of his thoughts came crashing together until there was only one thing left to say.

"I'm in love with you."

Cas was silent, and all Dean could hear was the thumping of his heart in his ears, and he was so nervous he started to shiver and shake, but he didn't regret saying it, even if Cas got up to grab his things and walk out right then, because at least he'd _said it_ , and that was all he'd ever wanted to do but couldn't for the last decade.

"Oh. Fuck," Cas said, breaking the silence. Dean felt his heart stop for a second, ready to break into pieces, but then Cas was surging forward, kissing him hard and crawling on top of him, and apparently that was the _good_ answer and not the _oh no, we can't do this_ answer. "Fuck, fuck, fuck," Cas was muttering against Dean's skin as he kissed down his chest, and Dean was really confused, but he wasn't about to stop him when he seemed to be headed right for his dick.

"Cas, is... is everything okay?" he asked, lifting up the blanket to try and watch as Cas wrapped a hand around his soft cock. It was too dark to see more than a big shape moving over his legs, but he could feel Cas smile as he pressed a kiss against his hip.

"Yeah, it's just, I don't think we can have sex like we just did for at least a day or two, but I've been dreaming of hearing you say that to me since the second week of freshman year, so I'm going to celebrate by giving you the greatest, most appreciative blowjob of your life."

"Oh. Okay," Dean said, not really sure what else to say. Tonight had gone far better than he'd ever thought possible, and he was suddenly, intensely afraid that it was a dream and he was going to wake up any second. But Cas' mouth felt real enough against his skin, and his fingers found their way down into Cas' hair, his fear already slipping out of him. But just in case, he added, "If this is a dream, don't wake me up. Ever."

Cas laughed and agreed, and one Best Blowjob of Your Life later, Cas was settled back against Dean's chest beneath the covers while Dean pressed kisses along his neck.

"Hey, Cas," Dean whispered, the feeling of Cas' stubble tickling his lips into a smile.

"Mm," Cas mumbled back, already drifting off.

"Happy Valentine's Day."

**Author's Note:**

> Dean and Cas were both eighteen and began attending the University of Kansas as freshmen in September of 1997, slept together on Valentine's Day in February 1998 (which was actually on a Saturday, not a Friday) and then met again on Valentine's Day in 2008. In 1998, Dean had an original Sony Playstation system (released in 1995) with assorted games, and a VCR with assorted movies on VHS (DVDs were introduced in the US in 1997 but didn't completely replace VHS tapes until 2002/2003). Enya, the artist Cas listened to, started her career as a singer in 1982 and had three Top 100 hits in the US before 2000. Her music, and Cas' other "weirdo music" as Dean called it, is from the New Age genre. The fic's title and first line of the summary comes from the name and lyrics of a Fleet Foxes song.
> 
> Aaaaand writing up these notes has made me feel like I'm writing a report for middle school, which is a bit awkward considering this "report" is full of gay porn, so I'm gonna stop now. Thanks for reading and happy (late) Unattached Drifter Christmas!


End file.
